This irrational and improbable thing actually happened: a comic strip titled Inside Woody Allen - starring the man himself - was syndicated by King Features from 1976 to 1984. Created and drawn by Stuart Hample of later Children’s Letters to God fame, the strip was based on Allen’s familiar persona—the angsty, neurotic, Jewish everyman if every man was a cripplingly overanalytical disaster—and it still got printed in daily newspapers for eight years!

I had a lightbulb epiphany. It occurred to me that Woody might make a terrific comic strip. But how would he – 39 and by now wildly successful – react? I ran a test scene in my head. Me: “Woody, I have an idea for a comic strip based on you. Possible?” Woody: “Sorry. Up to my neck writing a movie, editing another movie. Writing a piece for The New Yorker. Don’t need the money. Try me next year.”

So I asked him in person. Woody was intrigued enough to say: “Show me some sketches.” I based my drawings on how he looked in his late 20s, when we’d first met. He OK’d the Woody cartoon character (he even had it animated for a sequence in Annie Hall) and said: “What about the jokes?” I brought jokes. He looked through them. “Maybe,” he said, “I could help you with the jokes.”

Assuming he was offering to write them, I wanted to shout: “My saviour!” Instead, I said: “OK.” Which was more appropriate, since his help turned out to be dozens of pages of jokes from his standup years. Some were mere shards, such as “tied me to Jewish star – uncomfortable crucifixion”. Others were even more minimal: “bull fighting”, “astrology” (Woody occasionally translated these hieroglyphs).

But there were longer notations: “Sketch – man breaking up with female ape after his evolution.” And there were little playlets: “Freud could not order blintzes. He was ashamed to say the word. He’d go into an appetiser store and say, ‘Let me have some of those crepes with cheese in the middle.’ And the grocer would say, ‘Do you mean blintzes, Herr Professor?’ And Freud would turn all red and run out through the streets of Vienna, his cape flying. Furious, he founded psychoanalysis and made sure it wouldn’t work.”

A newspaper syndicate agreed to publish the feature. They requested six weeks of sample strips. I went each Saturday to Woody’s Fifth Avenue penthouse, where he judged the material and offered suggestions on how to develop characters and pace gags, and pleaded with me to maintain high standards. On 4 October 1976, the strip was launched. Woody, the pen-and-ink protagonist, was angst-ridden, flawed, fearful, insecure, inadequate, pessimistic, urban, single, lustful, rejected by women. He was cowed by mechanical objects, and a touch misanthropic. He was also at odds with his antagonistic parents; committed his existential panic to a journal; had regular sessions with his passive-aggressive psychotherapist; was threatened by large, often armed, men; and employed his modest size to communicate physical impotence the way Chaplin, in the guise of the Little Tramp, suffered humiliation.

I often wondered why Woody gave the concept a green light. In 1977, he related the following anecdote. He had cast the actress Mary Beth Hurt in his movie Interiors. Hurt regularly phoned her mother in Iowa to reassure her that she was safe and happy. During one of those calls, she proudly announced that she was going to play Diane Keaton’s sister in a movie “by somebody you probably haven’t heard of, a director named Woody Allen”. “I know about him,” said her mother, “he’s in the funny pages.” Woody’s manager figured it was no bad thing if his image was disseminated daily out in the heartland.

Read those again, and check out this small online gallery of strips, keeping in mind that these ran in the daily funnies. Children in the late 1970s and early 1980s were seeing gags about the dead bluebird of happiness alongside Marmaduke and The Family Circus. There are plenty of reasons that Gen X turned out so messed up, but might this strip be in that mix? Could this have been a contributor to our baffling consumption of shitty angst-rock and Fruitopia?

Much of that angst was attributable to Allen’s participation - and was of course necessitated by obeisance to his stand-up persona - but the most notable gag writer for the strip was David Weinberger, who later went on to a career as an online marketing guru, best known for his Cluetrain Manifesto and Small Pieces Loosely Joined. Interesting how Hample and Weinberger, the auteurs behind arguably the most openly neurotic and fussily intellectual daily comic strip ever syndicated in the United States went on to greater fame for such square stuff! I suppose angst is a less reliable cash generator than cute kids and formulae for success. So it goes.

Upon the 2009 release of Dread and Superficiality (not the only anthology of the strip, by the way, just the only one widely available presently), Hample appeared with Dick Cavett to talk about Allen and the strip at the fantastic NYC bookstore The Strand. There’s video, in five parts. Part 1. Part 2. Part 3. Part 4. Part 5.

For another amusing sample of Allen in an unexpected medium, check out this footage of him appearing opposite Nancy Sinatra on the game show Password in 1965.